An efficient asymmetric synthesis of manzacidin C

Kristy Tran; Pamela J Lombardi; James L Leighton

doi:10.1021/ol8011869

An efficient asymmetric synthesis of manzacidin C

Org Lett. 2008 Jul 17;10(14):3165-7. doi: 10.1021/ol8011869. Epub 2008 Jun 24.

Authors

Kristy Tran¹, Pamela J Lombardi, James L Leighton

Affiliation

¹ Department of Chemistry, Columbia University, New York, New York 10027, USA.

PMID: 18572947
DOI: 10.1021/ol8011869

Abstract

A brief synthesis of manzacidin C based on a chiral silane-promoted diastereo- and enatioselective acylhydrazone-alkene [3 + 2] cycloaddition reaction has been achieved. This synthesis is the first synthesis of any of the manzacidins wherein the C(4) and C(6) stereocenters are established in a single highly stereoselective step.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Cyclization
Molecular Structure
Pyrimidines / chemical synthesis*
Pyrimidines / chemistry
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Stereoisomerism

Substances

Pyrimidines
Pyrroles
manzacidin C